


boy problems

by superhoney



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Alternate Universe- No Supernatural, Bisexual Dean Winchester, Coming Out, Dean/Others along the way, Eventual Castiel/Dean Winchester, First Kiss, Fluff, Friends to Lovers, Growing Up, M/M, POV Multiple, POV Outsider, Referenced Cas/Others, See Author Notes for All Mentioned Pairings, your author thinks she is funny
Language: English
Status: Completed
Published: 2018-05-15
Updated: 2018-05-15
Packaged: 2019-05-07 10:53:58
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 7,978
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14669622
Author URL: https://archiveofourown.org/users/superhoney/pseuds/superhoney
Summary: Five times someone listened to Dean's relationship troubles and one time he listened to someone else's.





	1. Chapter 1

**Author's Note:**

> Just a short and sweet little character exploration and a bit of an experiment in using outsider POV.
> 
> Thank you to Ri for the advice and feedback! Look, I didn't even make you come up with a title for this one, Carly Rae Jepsen had it handled. 
> 
> Note: There are a lot of references to Dean being with/being interested in people who aren't Cas in this story. None of it is explicit, and Dean/Cas is the endgame, but if you're concerned, here is a complete list: OMC, Benny, Aaron, Jamie, Donnie, Lisa, and Cain. There are also brief references to Cas/Meg and Cas/OMC.

The front door slams, audible even over the music Mary has playing in the kitchen, and she switches off the radio with a frown. A few seconds later, the sound is repeated as Dean’s bedroom door shuts violently, and her frown deepens. Dusting off her hands, Mary climbs the stairs in search of her oldest son.

She knocks lightly on Dean’s door, and when there’s no response, pushes it open. “Dean?” she asks. “Honey, what’s wrong?”

Only the top of Dean’s head is visible, the rest of him covered by the blanket he’s pulled over himself. Mary crosses the room and perches on the edge of his bed. She reaches out to lay a hand on his shoulder, then draws back. He’s sixteen now, and though he’ll always be her sweet boy, she doesn’t want to baby him anymore. 

But this attitude is unlike him. He’s always so respectful, so helpful around the house. He has been for years now, ever since John walked out on them. Sometimes Mary wishes it weren’t the case, wishes he didn’t feel the need to step up in his father’s absence, but she’s always prided herself on raising her two boys well without John. 

“Dean?” she tries again, a little firmer this time. “We don’t have to talk about it. But I need to know you’re okay.”

With a heavy sigh, Dean pulls the blanket down and meets her eyes. “Sorry, Mom,” he mumbles. “I didn’t mean to take it out on the house.”

“This house has survived far worse,” she says lightly. “You want to tell me why you’re stomping around slamming doors?”

Dean’s gaze slides away from hers. “Just school stuff.”

It’s hard to conceal a smile at his classic evasiveness. “What kind of school stuff?” Mary prompts. “A bad test?” Dean takes his schoolwork so seriously, knowing he’ll need a scholarship to be able to attend college, and while Mary’s heart aches for the stress it puts on him, it also swells with pride every time he brings home another excellent report card.

“No,” Dean answers with another sigh. “But if Ethan doesn’t stop skipping all our study sessions, we’re going to flunk Biology for sure.”

Mary mentally flips through her catalogue of the boys’ friends. Charlie, Jo, Ava, Victor, Cas-- she knows all the usual suspects. But she doesn’t recognize the name Ethan. “Lab partner?” she guesses.

“Yeah.” Dean plucks at the hem of the blanket, still avoiding her eyes.

“Well, if he’s not putting in the effort, maybe you should ask your teacher if you can change partners,” Mary suggests.

“That’s what Cas said, but I think he just wants an excuse to try to convince Mr. Devereaux to let him ditch Marv, cause he’s been complaining about him all week.” 

“So why don’t you do that?” 

Dean shrugs. “Ethan’s on the basketball team, and they’ve got a good chance at the championship this year, and their coaches keep adding extra practices. It’s not like he wants to miss our study da-- sessions.” A flush rises in his cheeks, and he bites his lip, looking up at Mary with wide, panicked eyes. 

_Dates_. Study dates. That’s what Dean had been about to say. Suddenly, it all makes so much more sense. 

This is a big moment for both of them, and Mary is determined not to mess it up. God knows she has enough flaws as a mother, but she isn’t about to give Dean anything less than her full and unwavering support. 

“You really like him, huh,” she says. 

Dean just stares at her, his hands twisting tightly in the blanket. She waits patiently, and the longer she just sits there, holding his gaze, the more the fear in his eyes recedes. 

“You’re-- you’re okay with that?” he finally asks. Mary hasn’t heard his voice sound so small, so tentative, in six years. Not since he asked when John was coming back, and she had to tell him he never was. 

“Oh, sweetheart,” she murmurs. “I love you. And nothing is ever going to change that. Especially not something like this.”

After another long pause, Dean gives a shaky nod and launches himself into her arms. Mary wraps him in a tight hug, marveling at the solidity of him. He’s growing up so fast, but she’s so grateful that he still trusts her like this, still depends on her when he’s hurt or scared. She desperately hopes that never changes.

“So,” she says as he pulls away, “a basketball player.”

“He’s not just some jock, though,” Dean says quickly. “He’s really smart. It’s just tough for him to balance academics and athletics, you know? And the coaches don’t really get that, and they’ll bench him if he misses practice. He keeps saying how sorry he is every time he has to cancel on me, but--”

“But it’s hard not to take it personally,” Mary finishes. 

Dean nods. “I was so excited when Mr. Devereaux paired us up,” he admits. “But we’ve only been able to get together once so far.”

She knows Dean’s schedule isn’t always simple either. When she has an evening shift, he’s the one making sure he and Sam are fed, and she pushes aside the pang of guilt she feels about that. They do what they can with the circumstances, and she thinks they manage alright. She just wishes it could be easier on the boys sometimes.

“Well,” she says, thinking out loud, “Sam has to stay late on Wednesday for debate club, right? So you’re going to wait to walk home with him?”

“Yeah,” Dean answers, clearly puzzled as to what this has to do with Ethan or their Biology homework. 

“Do you know if Ethan has practice that day?”

“Probably.” Dean rolls his eyes. “I swear they have practice every day.”

“Why don’t you ask him if he wants to come over for dinner afterwards, then?” Mary suggests. “Since you’ll have to wait for Sam anyway. You can do your other homework in the meantime, and then you and Ethan can work here for the evening.”

She can practically see the gears turning in Dean’s head as he works through the plan. And when he grins up at her, Mary feels like punching the air in relief. Dean’s face is built for smiling, not for the misery she saw on it just a few moments before.

“You’re not going to like, interrogate him or anything, are you?” Dean asks. “Cause I don’t even know if he likes guys, Mom, so it’s not like I’m bringing him home for dinner in _that way_ or anything.”

“Relax, honey,” Mary laughs. “I’ll save that for the first boy-- or girl?” She pauses, unsure. Dean’s had crushes on girls before, Cassie and Robin and others. But now Ethan--

Dean goes pink again, but this time he holds her gaze. “Yeah,” he says. “I, umn, think I like-- girls and guys.”

“For the first _person_ you bring home in an official capacity, then,” Mary amends. “How’s that?”

“That sounds good,” Dean says. “Really good.”

She stands, squeezing his shoulder as she does. “Don’t you have other homework you should be doing?”

Dean rolls his eyes, but he’s still smiling. “Yes, Mom.”

Just before she leaves the room, he calls out after her. “Mom?”

Mary turns to look back at him. “Yeah, sweetie?”

“Thanks.” 

He shouldn’t have to thank her for anything. It enrages her that he feels like he does. But it’s not him she’s angry at, just a world that cares all too much about all the wrong things. So she just gives him a soft smile and says, “Of course.”

She shuts the door behind her, much more gently than Dean did earlier, and lingers in the hallway a moment before going back down to the kitchen to finish dinner. She’s never been much of a cook, but judging by the way both of the boys are growing, she’s feeding them well enough. She’ll have to remember to make more of an effort than usual on Wednesday. After all, this Ethan boy must be something special if he’s got Dean so worked up.

Mary turns the radio back on but keeps the volume at a reasonable level, conscious of Dean trying to study upstairs. But as the opening notes of a familiar song start to play, she can’t stop herself from singing along.


	2. Chapter 2

Sam pauses to thank the bus driver before disembarking, stepping out onto the University of Kansas campus with a bright grin on his face. Dean is waiting for him at the bus stop, and he pulls Sam in for a rough hug. “You made it,” he says.

“We’ve lived in Lawrence our whole lives, Dean, I know how to get to the college,” Sam points out, rolling his eyes.

“Yeah, well, whatever. I’m glad you’re here.” Dean is wearing a dark green KU hoodie and has a bulging backpack slung over one shoulder. He wraps his free arm around Sam and steers him through the crowds of people, heading for his dorm.

It’s nice, having Dean just a bus ride away even though he’s in college now. They talk all the time, but Sam misses having his brother around. Dean’s busy with classes and friends and all the other things Sam can’t wait to experience himself, but he still makes time to hang out with his little brother, and Sam’s grateful for that. 

“How’s Mom?” Dean asks as he swipes his keycard, holding the dorm door open for Sam. 

“She’s good. You don’t have to worry about her, you know.” Sam follows Dean up the stairs to the third floor, smiling shyly at the people who pass by in chattering groups. 

“Have you met me?” Dean scoffs. 

Sam rolls his eyes, but it’s more fondness than annoyance. “She sent you more socks, by the way. I don’t know why you couldn’t just get them the next time you come over for dinner, but she insisted I bring them today.”

“Best not to argue with Mom when she’s in a mood,” Dean advises. 

As they round the corner towards Dean’s room, his door swings open and a burly guy steps out, giving Dean a friendly smile and Sam an inquisitive look. “Oh, hey, Benny,” Dean says, running a hand through his hair. “This is my brother, Sam. I can’t believe you guys haven’t met yet.”

Sam instinctively sticks out his hand, and Benny takes it in a firm grip. “Nice to meet you, Sam,” he says. “Heard a lot about you.”

“Yeah, you too,” Sam replies. Benny hadn’t arrived yet when Sam and Mary helped Dean move into the dorms, but he’s been a constant thread in Dean’s updates about college life. It’s nice to finally put a face to the name.

“You heading out?” Dean asks Benny, sounding almost disappointed. “Woulda been nice to hang out.”

“Yeah, taking Andrea out for coffee,” Benny says with a wink. “All my smooth talking finally paid off.”

Dean smiles, but Sam knows him well enough to tell that it’s fake. “Nice,” Dean offers. “Well, some other time.”

“You bet.” Benny gives Sam a cordial nod, then strides off down the hall, whistling cheerfully.

Sam crosses his arm over his chest as Dean opens the door to his room and waves him inside. “So, that’s Benny.”

“Yeah,” Dean replies. “Too bad he couldn’t stick around, would be nice for you guys to get to know each other.”

“And that’s the only reason it’s too bad he couldn’t stick around?” They only get to see each other once a week, so Sam figures he can up the ante on the annoying little brother routine. It’s only fair.

“What?” Dean is carefully avoiding his gaze, sweeping papers off his desk and dropping his backpack on the ground with a heavy thud. “What are you talking about?”

“You like him, don’t you?” It’s so immediately, painfully obvious. For all his pretended cool, Dean has always been kind of a mess around people he likes, especially guys. 

“Shut up,” Dean replies, which might as well be a yes. 

Sam settles back on Dean’s narrow bed. “And I’m guessing he doesn’t feel the same, considering how excited he was about going for coffee with whoever Andrea is.”

Dean sighs and slumps into his chair, leaning his chin on its back. “Got it in one.”

“That sucks,” Sam offers. He’s not exactly an expert in relationships, but he’s pretty sure it can’t be fun to watch the person you like go off on a date with someone else. 

“Yeah, just a bit. And because I’m a good friend, I have to be supportive and encouraging and ask him how it went, and pretend to be happy for him if they get together for real, and--” Dean suddenly stops, a look of horror crossing his face. “Oh my god, what if I get sexiled?”

Sam just blinks at him. “What if you get-- what?”

Dean waves a hand at him. “Don’t tell Mom I talked to you about this. You’re fourteen, you’re old enough. Sexiled. Kicked out of the room so the other person can have sex.”

“Oh.” Sam wrinkles up his nose. “That sounds kinda mean.”

“You’ll understand someday, Sam,” Dean says distantly. 

“Can we go back to the not-sex part of the conversation?” Sam asks with a shudder.

Dean sighs. “It’s fine,” he says. Which means it absolutely isn’t. “I just have the worst luck in the universe and somehow developed a crush on my roommate. They don’t exactly cover that in the freshman handbook, you know? God, I should have just roomed with Cas like I wanted to.”

“Even I know you’re not supposed to room with your best friend in college,” Sam reminds him. “It never ends well.”

“Yeah, well, it would probably be better than this,” Dean mutters.

Sam doesn’t really know what else to say. Dean’s always a bit dramatic about this kind of thing, but underneath all that is what seems to be genuine hurt. “He doesn’t know, does he?” he asks.

Dean’s head flies up. “God, no,” he says vehemently. “I mean, I sure as hell hope not.”

“So he’s not deliberately hurting you,” Sam concludes. “Good.”

“What, like you’re going to beat him up for me?” One corner of Dean’s mouth lifts in a small smile. “You’re like half his size, Sammy.”

“Not everything is solved with physical violence, Dean. I just meant, he seems like a good guy. But that doesn’t mean he’s the only one out there, you know?” 

“Are you really trying to give me the plenty more fish in the sea line?” Dean shakes his head. “Weak.”

Sam throws his hands up in the air. “Well this is what you get when you ask a fourteen year old for advice.”

“Never asked,” Dean mutters, but then he exhales loudly. “You know what? Let’s just-- forget about it. This isn’t what you came to visit me for.”

There’s no point arguing with him. If Dean decides he’s done talking about something, he’s done. So Sam just nods and rises to his feet. “Can we go get milkshakes at the student centre?” he asks. “I’ve been dreaming about that strawberry banana one since the last time I was here.”

“Yeah, sure,” Dean says. He picks his keycard back off the desk, and even with his back turned, Sam can see the way he gathers himself. By the time he turns to face Sam once more, his grin is back in place. “What is that line? Something about milkshakes bringing all the boys to the yard?”

Obviously, the time for earnest conversation has passed. So Sam just shakes his head, sticks his nose in the air, and says, “Gross, Dean.” If that’s what Dean needs right now, the comfort of familiar rhythms, then that’s the least Sam can give him.


	3. Chapter 3

Charlie drums her fingers on the tabletop, checking her phone for what feels like the fifth time in as many minutes. Dean is never late. It’s one of the things she appreciates most about him, along with his ability to understand all of her references and his usefulness in reaching objects above her head. They meet for coffee every Tuesday morning at 10:00, and it’s now 10:10, and she’s starting to get a bit worried.

So she does what any good friend would do and sends a concerned text. _Dean Winchester, if you do not get your ass here in the next five minutes with a damn good excuse for being late, I’m demoting you from the rank of Handmaiden._

Not thirty seconds later, Dean slides into the seat across from her, hands already rising to cut off her righteously indignant commentary. “I know, I know,” he says. “I’m sorry I’m late.”

Charlie crosses her arm over her chest. He looks slightly rumpled, but not in any sort of mortal peril. “Check your phone.”

Dean frowns at her, but doesn’t dare refuse a direct order. He pulls out his phone and reads her message, his shoulders shaking in silent laughter. “Oh come on, Your Majesty,” he says. “You know you’ll never find another handmaiden like me.”

He has a point. Dean’s enthusiasm for their LARPing group is matched only by her own. “I still want that excuse,” she says. 

Dean flushes slightly. “Let me get caffeine first,” he begs. “Then I promise I’ll tell you everything.”

Charlie waves a hand in her most magnanimous manner. “Very well.”

She flips through her phone while Dean gets their usual beverages, and as soon as he returns to the table and passes over her mocha, she puts it away and gives him her full attention. “Okay, Winchester. Spill.”

Dean sighs and takes a sip of his coffee before responding. “So, I was out last night,” he starts. “All night.”

Reflexively, Charlie reaches out for a fistbump. “Not a good enough excuse,” she says, “but intriguing enough to distract me. Who’s the lucky person?”

“His name is Aaron,” Dean says. “We have a few classes together, and we were studying last night, then it kinda just--” He shrugs loosely. “Stress relief, you know?”

“Still doesn’t explain why you were late. What, did he make you breakfast or something?” He doesn’t have that starry-eyed look he sometimes gets, but Dean is being unusually cryptic about the whole thing. They’re normally pretty open with each other about their hook-ups. 

“No, nothing like that,” Dean says quickly. “I had to run home and get changed, that’s all. That’s why I’m late.”

Charlie raises her mocha to her lips and looks at him over the edge of the cup. “Are you going to see him again?”

Dean visibly deflates, slumping back in his chair. “I don’t know,” he says. “I don’t know if I want to.”

“Ouch,” Charlie says with a wince. “That bad?”

That at least makes him smile. “No, no. It was fine. Good. I just--” He shrugs again. “I like hanging out with him, and we had fun, but there’s no real spark, you know?”

“So, what, you just slept with him because it seemed like more fun than studying?”

“Charlie!” Dean practically hisses, looking around the quiet cafe. “A little bit more tact, please?”

It’s funny, when he suddenly gets all delicate like this. It brings her great joy to rile him up. “Oh please,” she says. “Like they haven’t heard it all before.”

Dean continues to scowl at her, pitching his voice slightly lower as he goes on. “It wasn’t like that,” he insists. “But it’s not like we’re going to be spending all our nights together from now on either.”

“Nothing wrong with a one and done,” she tells him, raising her cup in a toast. “You know that. So what’s got your panties in a twist?”

“Please,” Dean says without skipping a beat, “he wouldn’t get to see those until at least the third date.”

Charlie nods approvingly. “Gotta keep surprising them,” she says. “But seriously. What’s with all the drama?”

Dean stares moodily into his coffee cup like he’ll find some sort of answer there. “I’m just kind of sick of it.”

“Sick of sex?” Charlie asks incredulously. That’s a new one.

“What? No.” Dean shakes his head. “God, no. Just-- the whole awkward morning after thing, where you don’t want to presume anything but you don’t want to make the other person feel bad, so you just say it was fun and whatever and nothing is ever really settled.”

“What a shock, Dean Winchester has communication issues,” she says. There’s no real heat to her words, though, and fortunately Dean knows her well enough not to be hurt by the comment. 

“It’s hard to communicate what you want when you don’t even know what you want, though,” he points out. 

“Fair.” She drums her fingers on the table again. “What do you think he wants?”

“I don’t think he’s looking for anything serious,” Dean replies. “So I don’t have to worry about feelings getting hurt if this is all it’s ever going to be.”

“Well thank god for that,” Charlie says with a shudder. “We do not need a repeat of the whole Cas and Meg shitshow.”

Dean winces. “Yeah, that was a mess. But Aaron is a lot more chill than Meg, so I don’t think we’re going to have that kind of problem.”

“So what kind of problem do we have?” Charlie asks. “I’m still not really sure.”

“Me neither,” Dean says with a laugh. “Maybe-- the problem is that there is no problem?” He seems amazed at the idea. “Charlie, am I making this into a much bigger deal than it really is?”

“Absolutely,” she tells him. “Finally, you get it. I was waiting for you to figure it out.”

“You could have just told me.” Dean frowns at her. “Instead of dragging it out this way.”

“That isn’t a very effective leadership strategy,” she tells him smugly. 

Dean shakes his head at her. “Have I told you that I love you lately?” he says, pressing a dramatic hand to his chest.

Charlie just smiles at him and takes another sip of her mocha. “I know,” she says.


	4. Chapter 4

It’s Friday night, so the place is packed. Jamie doesn’t mind, though. She’s been tending bar at this hole in the wall just off the KU campus for a few years now, and there isn’t much left that can faze her. The college kids are generally manageable, as far as bar patrons go. Most of the time they’re too poor to ever get completely wasted, but they tip reasonably well, knowing how tough it is to work this kind of job. 

She sees a familiar figure enter and starts pouring a beer before Dean has even reached the bar. He manages to find an empty stool, and she slides it over to him just as he sits down. “You’re the best,” he says with a grateful smile, raising the glass in a salute. “Busy night, huh?”

“Very,” she replies, already busily mixing a round of mojitos for the girls in the corner booth. “Nice of you to come by on your own, keep our numbers down.”

Dean has been a regular here for some time now, but he’s usually got at least one other person with him. Charlie, or Cas, or even Benny. She studies him from across the bar as he sips his beer, his eyes wandering around the room as though he’s looking for someone in particular.

“Are you meeting someone here?” she asks, propping her elbows on the surface of the bar. “Who? I can let you know if I’ve seen them.”

“No, no.” Dean waves a dismissive hand in the air. “Just checking if anyone I knew was here.”

Jamie is called away to the other end of the bar by someone shouting for tequila shots, so it’s a few minutes before she has the chance to pick up the conversation with Dean. He’s halfway through his beer, and he still looks like he’s waiting for something, or someone.

So she pours him another beer, and when he looks up to thank her, his usual charming grin is back in place. Jamie has been on the receiving end of that brilliant smile a few times, and one time it even worked on her. They went home together that night, had a great time, and have never spoken about it since. 

So she’s understandably wary about the fact that he’s here alone and giving her that look now. She likes Dean, she really does, but she’s not looking to get involved with anyone. Better to shut this down, and quickly.

“Dean, if you came here tonight thinking we could go for a repeat performance--” she starts, but his eyes open so comically wide she knows she read this whole thing wrong.

“No, no, no,” he assures her. “I mean. Don’t get me wrong, you’re great, and you’ve got a pretty-- everything.” He gestures loosely at her face and hair and possibly her chest. “But no. I’m not hitting on you, I swear.”

“Well, good,” Jamie says, still a bit thrown. She can handle guys being interested in her. It’s pretty much a requirement of the job. But this is a new one. 

Before she can dig for more details, though, she gets called away again. Somebody is having trouble with their credit card, somebody else offers to cover them, then someone else buys a round of shots in celebration of their generosity, and it’s all such joyful chaos that it only highlights the misery on Dean’s face as he sits alone at the far end of the bar.

Fortunately, she’s due for a break, so she slips off her apron and pours herself a soda, then grabs a spare stool and pulls it around to the side of the bar. “Okay,” she says to Dean. “Talk to me.”

“You get enough sad sacks spilling their secrets to you, you don’t need to hear that from me.” He laughs, but there’s no humour in it. “I should just head home. This was a waste of time.”

“You’ve still got a half a beer,” Jamie points out. “And you can’t leave me to spend my break alone. That would just be rude.”

“And lord knows I could never be rude to a lady like you.” Dean sighs. “Alright, fine.”

“So are you going to tell me what’s got you looking like a kicked puppy?” she asks. “Trouble at home?”

“No, no. Mom’s great, Sam’s still kicking ass out at Stanford, we’re about as happy as we’ve ever been.” 

“So school, or love life,” she states. And when she sees Dean wince, she knows she’s hit the nail right on the head. “You were looking for someone tonight, weren’t you?”

“You’re really persistent, has anyone ever told you that?” Dean says, shaking his head at her.

“Yes,” she answers. “Right before they gave me what I wanted.”

This time, his laugh is more genuine. “Alright,” he says, taking a deep breath. “Yeah, I was hoping to run into someone here tonight. But not out there.” He nods towards the main area of the room. “Back here.” He taps the side of the bar.

Jamie frowns at him. It’s a small place, and they’ve only got four bartenders on staff. Besides herself, there’s Tessa, who’s happily married, Jake, who’s working tonight so can’t be the one Dean wanted to see, and--

“Donnie?” she asks, raising one eyebrow in interest. 

Dean flushes, but nods. “He’s been here most Fridays, so I guess I just thought… I don’t know.” He runs a hand through his hair. 

“Sorry, hon,” Jamie says, and she means it. “He and Jake switched shifts. Jake has a wedding to go to tomorrow, so Donnie said he didn’t mind working the Saturday night instead.”

Dean’s face brightens so quickly Jamie nearly gets whiplash. “So he’ll be here tomorrow, then?”

Biting back a laugh at his abrupt change in mood, she reaches out and pats him on the shoulder. “Barring any sort of illness or injury, yeah. What, are you going to grace us with your presence two nights in a row?”

“Absolutely,” Dean says. “I actually already had plans to meet Charlie and Cas here tomorrow night. But I didn’t think Donnie would be here then, so I came tonight too.”

“Well, sorry you got stuck with little old me,” Jamie says dryly. 

“I’m not,” Dean says, and it’s the rarer smile this time, the one that’s all sweetness and sunshine without any sort of calculated charm. He drains the last of his beer, slides way more cash than is appropriate for his two drinks across the bar, and gives her a wink. “I should head home and get some beauty sleep if I’m going to stare longingly at Donnie from across the room all night tomorrow.”

“Or you could just, you know, ask him out,” Jamie suggests. 

“Maybe someday,” Dean says in a tone that implies that day will never come. “See you tomorrow?”

“I’ll be here,” Jamie replies. She shakes her head fondly as Dean pulls his leather jacket back on and heads for the door, holding it open for a group of girls who are just coming in. He gives her one last wave, which she returns, and then he’s gone. 

Jamie finishes the rest of her soda in one long swallow, then sets the glass down with a smile. At least she has something to look forward to tomorrow night. But for now, there are more drinks to pour, more tips to be made, and more people to lend a sympathetic ear to. A bartender’s work is never done.


	5. Chapter 5

Lisa is pushing Ben on the swings despite his insistence that he doesn’t need her help anymore. At four, he’s starting to discover the concept of independence, and as much as it sends a pang through her heart when he says he can do it alone, it amuses her when he realizes he can go higher with her pushing him. 

“Mom!” he yells as he swings back towards her. “Stop, stop!”

Panicked, Lisa grabs the chains and holds the swing steady, eyes scanning over his body, checking for injuries. But Ben is already out of his seat, tearing across the playground towards a tall figure waving enthusiastically at him.

She should have known. Shaking her head, Lisa waits patiently as Ben dashes over to Dean, launching himself into a hug that’s more of a tackle. Dean picks him up and settles him on his shoulders, then walks back over to where Lisa is standing, Ben chattering away the whole time.

“Hey, Lis,” Dean says, giving her a quick kiss on the cheek. “How’s it going?”

“Good,” she answers, barely able to get a word in over Ben’s monologue. “Ben, why don’t you get down from there? Dean’s getting old, don’t want to strain his shoulders.”

Dean rolls his eyes, while Ben pouts and sighs, but their expressions are so similar in that moment that Lisa almost wants to call her doctor and schedule a second paternity test. Dean may not be Ben’s biological father, as she once thought he might be, but Ben has certainly picked up a number of his mannerisms over the years. 

There are far worse people who could have that kind of effect on her kid, she supposes. 

Dean gently sets Ben down, and Ben tugs at his hand and drags him back over to the swings. “You can push me even higher than Mom can!” he exclaims in delight.

It’s Lisa’s turn to roll her eyes. “Oh, I see how it is,” she jokes. “Guess you don’t need me anymore.”

“We totally do,” Dean insists. “You can be our cheerleader.”

“In your dreams,” she mutters, too quietly for Ben to hear. Dean catches it, though, and gives her a playful wink. 

They chat lightly as Dean continues to push Ben on the swing. Lisa catches more than one mom sending admiring glances at Dean, at the way his forearms flex, the way his grin curls up the corners of his lips. She can’t say she blames them, and a small, smug part of her is pleased at their quiet envy, noting that none of their partners are with them. Not that she considers Dean _hers_ in any way. They had one incredibly satisfying weekend together almost five years ago, but neither of them is looking to rekindle anything.

A few minutes later, a tug on Lisa’s hand draws her attention away from Dean. She looks down to see Ben’s friend Kiera smiling up at her. “Hey, sweetie,” she says. 

“Can Ben come play tag?” Kiera asks.

Dean grabs the chains of the swing so Ben can see his friend. “What do you think, buddy?” Dean asks. “You just say the word.”

Ben mulls it over for a moment, then hops down from the swing and tears off across the park, Kiera following after him. Dean chuckles and makes his way over to a bench where they can easily keep an eye on the kids, patting the space beside him.

“Come on,” he says. “We’re long overdue for a grown-up talk, Braeden.”

He rests on arm on the back of the bench, almost as though he’s putting it around her, and Lisa feels the eyes of the other moms on them once more. “Are you doing this on purpose?” she murmurs. “That woman is giving you heart eyes and me dagger eyes. It’s amazing she can go back and forth so easily.”

Dean grins at her, mischievous as always. “Maybe,” he admits. “It’s pretty sad that my main source of fun these days is riling up the moms at the playground, but you have to admit, it’s pretty funny.”

“It is,” she agrees. “Both funny and sad.” She pokes him lightly in the chest, and he swats her hand away, both of them laughing. “Really, though. No other source of fun?” She puts a deliberate emphasis on the last word and enjoys the way it makes the tips of Dean’s ears flush pink. For all his charm, he’s always been hilariously easy to fluster.

“There was something,” he admits quietly. “But I think I’m going to end it.”

There’s genuine sadness in his voice, and Lisa immediately drops her teasing tone. “How come?”

Dean looks around as though making sure no one can overhear them before continuing. “He’s a great guy, really. I like him a lot, and most of the time, things are good. He’s older, and he knows what he wants, so he isn’t into playing games like so many people our age are.”

“Nice,” Lisa says approvingly. “Grey hair?”

“Definitely.” A distant look enters Dean’s eyes, then he shakes it off. “Cain’s great. Really.” He sounds like he’s trying to convince himself just as much as he is Lisa. 

“So what’s the problem, then?”

Dean sighs. “Most of the time, I don’t notice the age difference, or think it’s a bad thing. I mean, I’m twenty-five, I’m an adult. But sometimes it’s like he blames it for anything we disagree on, and I can practically hear him saying he must be right because he’s so much older and wiser than me.”

Lisa crinkles her nose up in distaste. “Gross.”

“It’s not the end of the world,” Dean says. “And I really do like him. But--”

“But you deserve to be with someone who treats you like an equal.” Lisa gives him a gentle smile, nudging him with her shoulder. “Don’t you dare think of settling for anything less, Winchester.”

That brings a smile back to his face, and Lisa’s happy to see it. “Okay, boss,” he says, rolling his eyes. “It’s funny, that’s pretty much exactly what Cas said, too. So if the two smartest people I know are telling me to do something... I guess it’s better to end it sooner rather than later, huh.”

“Definitely. Less chance of heartbreak all around.” 

“Thanks, Lis.” He smiles at her again, but his eyes are still sad. As much as Lisa knows they’re better off as friends, she wishes she could be the one he’s looking for. Wishes she could give him what he needs. But she can’t, so this is what they have: honest conversations while her son plays nearby, mutual support and a friendship that means the world to her.

“You’re going to find it, Dean,” she tells him. “The kind of relationship you want. I know you will.”

He raises an eyebrow at her, always too good at reading her tone. “You sound like you’re speaking from experience.”

Lisa tries to brush it off, but Dean’s eyes widen in glee, turning to face her more fully. “Are you dating someone?”

There’s no distracting him now. So Lisa sighs and gives in, telling him all about Matt and the two dates they’ve been on so far, how good he is with Ben and how much she likes him. Dean’s smile only grows as he listens, and when she finishes, he gives a sharp nod. 

“I better get to meet him soon,” he says, crossing his arms over his chest. “Make sure he’s good enough for you.” His eyes wander back over to where Ben is still playing with his friends, and they go soft and fond. “For both of you.”

“Dork.” Lisa leans over and presses a kiss to his cheek, letting it linger so the other moms really get a show. “As long as I get to do the same for the next person you date once you dump this old fart.”

“Deal,” Dean replies, and that’s that.


	6. Chapter 6

Castiel stares at his phone, willing it to light up with a new notification. But it remains blank, and he tosses it aside with a sigh, reaching for his wineglass instead. He’s thankful to his past self for deciding to go ahead and order a drink while he waited, because it’s looking more and more like he’s been stood up.

His date is over half an hour late, and hasn’t replied to Cas’ polite text checking in with him, sent twenty minutes ago. For a brief moment, he worried that something terrible had happened, but a quick conversation with Charlie informed him that Josh was alive and posting on social media, so clearly tragedy wasn’t an excuse.

The only tragedy here is Castiel’s appalling lack of luck in the dating department, as always. 

At least the restaurant is nice, a trendy but unpretentious little place serving classic fare with a modern twist, with an extensive selection of wines and local craft beers. Castiel just wishes he had someone to share it with. 

His phone chimes at him, and he grabs it eagerly. But the text isn’t from Josh, it’s from Dean. 

_Hey Cas, I know you’re out at dinner, but I just found your KU hoodie in with my laundry. You must have left it behind last time you were over. Let me know when you want to pick it up._

Cas pauses for a moment, then types out a reply. _Or you can come join me for dinner and bring it with you. I think I got stood up._

_See you in fifteen_ Dean sends back almost immediately.

Always so reliable. Feeling about a thousand times better than he did five minutes earlier, Cas drains the last of his wine and peruses the menu, already having a hard time deciding what he wants to try.

Approximately seventeen minutes later, Dean slides into the seat across from him and props his chin on his hands, his jaw tight. “Who do I have to murder?” he asks.

“Hello, Dean,” Castiel says mildly. “How are you tonight, other than frighteningly homicidal?”

“Don’t change the subject,” Dean says. “What kind of asshole just bails on a date?”

Cas shrugs, warmed by Dean’s outrage. “The kind who won’t be getting another one, I suppose.”

Their server stops by to get their drink orders, and it’s mesmerizing, how quickly Dean goes from coldly furious to warm and charming. He orders himself a beer, but Cas decides to stick with wine, though it makes Dean crinkle up his nose in distaste. It shouldn’t be such an adorable expression on a twenty-seven year old man, but it is. 

Dean takes a sip of his beer, makes a pleased noise, then takes another. But his eyes are serious as he looks over the top of his glass at Cas. “You okay?” he asks.

The concern in his voice is what proves Cas’ undoing. He sighs heavily, running one hand through his hair. “I really thought this one might work out,” he admits. “I know it was only going to be our second date, but I really liked him.”

If he’s being entirely honest with himself, the blow to his pride is what hurts the most. To not even be worth cancelling on, but just left hanging, waiting on someone who doesn’t even care enough to bother with a courtesy text. 

“I’m sorry, Cas,” Dean says gently. “But if it makes you feel any better, it’s probably good that he showed his ass now, rather than stringing you along and hurting you worse later.”

“Yeah,” Cas agrees. “You’re right. It’s just so frustrating. I finally meet a guy who seems worth pursuing something with, and then this happens. It makes me want to give up on dating altogether.”

“You’re a dramatic little shit, have I ever told you that?” Dean grins at him from across the table. “Don’t give up just because of one asshole.”

“But that’s the problem!” Cas waves his hands wildly. “It’s not just Josh. It’s every person I’ve dated or been interested in, one after the other. It never works out, and here I am, twenty-seven and reasonably successful, going home alone to my cat. I guess that’s not interesting enough to warrant a second date.”

“I wouldn’t call having two published novels only reasonably successful, but okay,” Dean says with a shrug. “And your cat is awesome.”

“You’re right about that, at least,” Cas mutters. “You’re also insufferably cheerful, did you know that? I invited you here to commiserate, and instead you’re being all encouraging and supportive.”

“Well, gee, Cas, guess I missed the memo.” Dean rolls his eyes, but his exasperation is clearly faked. “I’m not going to sit here and let you beat yourself up, all right? You’re awesome, Cas. And anyone who can’t see that is missing out.”

“It would seem the whole world is missing out, then,” Cas says, staring moodily into his wine glass. “I swear I’ve run through the entire list of eligible singles in the greater Lawrence area, all to no avail.”

“Not quite,” Dean remarks. There’s something strange in his voice, something Cas can’t quite pinpoint. He looks up, frowning, as Dean takes a deep breath and squares his shoulders.

“There’s still me,” he says.

Cas blinks at him in surprise. His mouth opens, but no words emerge. Fortunately, he’s spared having to reply immediately by the arrival of their meals. Once the food is in front of them, though, and their server has left, he pulls his lower lip between his teeth and considers Dean from across the table.

They’ve known each other for so long-- almost fifteen years now. Sure, there were moments when Cas wished they could move past friendship. Moments when Dean would say something particularly funny and make Cas laugh like no one else could. Or moments when the sun would hit his eyes just right and Cas’ breath would catch in his throat at how green they looked in that light. Or the quieter moments, when Cas would call Dean in the middle of the night, panicking about something to do with his books, and Dean would stay on the phone with him until he fell asleep. 

Dean waits patiently under his gaze, the nervous set of his shoulders the only indication that he’s just completely changed the course of their relationship. No matter what Cas says, this is a turning point for them. 

So he considers his words carefully before replying. “Are you saying you want to date me?” he asks.

A small, slightly embarrassed smile plays around Dean’s lips. “Cas, I’ve wanted to date you for years,” he admits. “I never thought you were interested, but you asked me here tonight, and I thought, fuck it. Why not give it a try?”

“Years?” Cas echoes, frowning. “Dean, you’ve dated...how many people in that time? Forgive me, but it doesn’t sound like you were pining away for me or anything.“

“You were dating other people too,” Dean points out. “And they’ve all let you down. Lord knows I haven’t been too lucky in love either. But Cas--” he spreads his hands before him--”look. We get along great. We know everything there is to know about each other. I was the first person you asked to come here tonight after you got stood up. That’s gotta count for something, right?”

“It does,” Cas agrees, “but is it enough to build a relationship on?”

He doesn’t know why he’s being so hesitant. Honestly, the thought of dating Dean, of being with him in every sense of the word, is as thrilling as it is terrifying. 

Dean lowers his voice slightly. “If it helps, I’ve definitely imagined sitting across from you just like this, except maybe with a little bit of risqué hand-holding involved.” He winks, and Cas’ heart gives a funny little flip in his chest, and he gives in.

This is right. He knows it.

“Is this our first date, then?” he asks, and is rewarded with a smile so dazzling Cas feels lightheaded. Though that might also be due to the wine. 

“I believe it is,” Dean replies. He picks up his beer glass and raises it towards Castiel in a toast. “Here’s to us.”

“Here’s to us,” Cas echoes. How strange. 

It’s kind of amazing, how easy it is to go on with the night even after that life-changing moment. They talk the way they always have, they split dessert the way they always have, and they argue over the bill the way they always have. When they leave the restaurant, Cas slides into the passenger seat of Dean’s Impala like he belongs there, because maybe he does, maybe he always has. 

But when Dean pulls up in front of his apartment building, Cas gives him a sidelong look and says, “Do you want to come inside?” in a tone of voice he’s never used with Dean before. And Dean swallows roughly, his eyes darkening, and follows Cas up to his apartment, one large hand resting lightly at his waist, its warmth tangible even through his clothing. 

Dean moves around the apartment with familiar ease, hanging his jacket in the closet and putting his shoes away so the cat won’t try to steal them. Cas watches him with a fond smile on his face, and when Dean turns back to face him, he lays a gentle hand on his shoulder and pulls him closer. Dean smiles, and Cas closes the distance between them, and any lingering doubts he might have had are erased by their kiss.

Later, much later, when they’re sprawled across Cas’ bed, wearing nothing but their boxers, Cas rolls over onto his side and looks down into Dean’s face. “You know,” he muses, “this means I’m going to have to find someone else to complain about my love life to.”

Dean frowns at him, and Cas laughs, kissing it away. “You’re not going to have anything to complain about,” Dean mutters darkly. “But on the off-chance that you do, I’ve got a whole list of people I know who are great at listening to exactly that kind of thing.”


End file.
